Please do not adjust margins
Organic & Biomolecular Chemistry
Page 5 of 5
DOI: 10.1039/C8OB00500A
Journal Name
5
ARTICLE
(a) T. Bock, H. Möhwald and R. Mülhaupt, Macromol. Chem.
Phys., 2007, 208, 1324; (b) F.-M. Hsu, C.-H. Chien, C.-F. Shu,
C.-H. Lai, C.-C. Hsieh, K.-W. Wang and P.-T. Chou, Adv. Funct.
Mater., 2009, 19, 2834; (c) O. R. Evans, D. R. Manke and W.
Lin, Chem. Mater., 2002, 14, 3866; (d) S. M. Zakeeruddin, M.
Abe and T. Yamagishi, Tetrahedron, 2015, 71, 7614; (d) X.
Zhang, H. Liu, X. Hu, G. Tang, J. Zhu and Y. Zhao, Org. Lett.,
2011, 13, 3478; (e) C. Shen, G. Yang and W. Zhang, Org.
Biomol. Chem., 2012, 10, 3500; (f) Q. Yao and S. Levchik,
Tetrahedron Lett., 2006, 47, 277.
K. Nazeeruddin, P. Pechy, F. P. Rotzinger, R. Humphry-Baker, 13 (a) S. Sengmany, E. Léonel, F. Polissaint, J.-Y. Nédélec, M.
K. Kalyanasundaram, M. Grätzel, V. Shklover and T. Haibach,
Inorg. Chem., 1997, 36, 5937; (e) S. Edizer, G. Sahin and D.
Avci, J. Polym. Sci. A: Polym. Chem., 2009, 47, 5737.
Pipelier, C. Thobie-Gautier and D. Dubreuil, J. Org. Chem.,
2007, 72, 5631; (b) S. Sengmany, E. Le Gall and E. Léonel,
Molecules, 2011, 16, 5550; (c) S. Sengmany, A. Vitu-
6
(a) Q. Dang, Y. Liu, D. K. Cashion, S. R. Kasibhatla, T. Jiang, F.
Taplin, J. D. Jacintho, H. Li, Z. Sun, Y. Fan, J. DaRe, F. Tian, W.
Li, T. Gibson, R. Lemus, P. D. van Poelje, S. C. Potter and M.
D. Erion, J. Med. Chem., 2011, 54, 153; (b) P. Lassaux, M.
Thiebaud, E. Le Gall, S. Condon, E. Léonel, C. Thobie-Gautier,
M. Pipelier, J. Lebreton and D. Dubreuil, J. Org. Chem., 2013,
78, 370; (d) S. Sengmany, S. Vasseur, A. Lajnef, E. Le Gall and
E. Léonel, Eur. J. Org. Chem., 2016, 4865.
Hamel, M. Gulea, H. Delbrück, P. S. Mercuri, L. Horsfall, D. 14 To the best of our knowledge, this is the first example of a
nickel-catalyzed phosphonylation reaction preserving such
aromatic C-Cl bond.
Dehareng, M. Kupper, J.-M. Frère, K. Hoffmann, M. Galleni
and C. Bebrone, J. Med. Chem., 2010, 53, 4862; (c) K.
Moonen, I. Laureyn and C. V. Stevens, Chem. Rev., 2004, 104
,
15 Addition of pyridine to the medium revealed beneficial
effects in related reaction systems involving heteroaryl
halides. For details, see: R. Rahil, S. Sengmany, E. Le Gall and
E. Léonel, Synthesis, 2018, 50, 146.
6177; (d) R. Engel, Chem. Rev., 1977, 77, 349; (e) C. Liu, S. G.
Dumbre, C. Pannecouque, C. Huang, R. G. Ptak, M. G.
Murray, S. De Jonghe and P. Herdewijn, J. Med. Chem., 2016,
59, 9513; (f) S. J. Hecker and M. D. Erion, J. Med. Chem., 16 It can be noted that the formation of transient NiI species
2008, 51, 2328; (g) V. Pham, W. Zhang, V. Chen, T. Whitney,
J. Yao, D. Froese, A. D. Friesen, J. M. Diakur and W. Haque, J.
Med. Chem., 2003, 46, 3680; (h) J.-J. Shie, J.-M. Fang, S.-Y. 17 No cross-coupling occurs when the reaction is performed in
has already been reported by our group in reductive
couplings involving aryl or heteroaryl halides, see ref. (13c).
Wang, K.-C. Tsai, Y.-S. E. Cheng, A.-S. Yang, S.-C. Hsiao, C.-Y.
Su and C.-H. Wong, J. Am. Chem. Soc., 2007, 129, 11892.
(a) M.-N. Birkholz, Z. Freixa and P. W. N. M. van Leeuwen,
Chem. Soc. Rev., 2009, 38, 1099; (b) M. McCarthy and P. J.
Guiry, Tetrahedron, 2001, 57, 3809; (c) W. Tang and X.
Zhang, Chem. Rev., 2003, 103, 3029; (d) D. S. Surry and S. L.
Buchwald, Chem. Sci., 2011, 2, 27; (e) H. Fernández-Pérez, P.
Etayo, A. Panossian and A. Vidal-Ferran, Chem. Rev., 2011,
111, 2119.
a divided cell or with non oxidable anode materials like
platinum or graphite. In addition, it was found that after 3 h
electrolysis (2160 C), the anode has lost 490 mg (approx. 8.6
mmol) of its mass and conversely, the cathode has gained
440 mg of its mass. The major part of the electrogenerated
metal salts is reduced at the surface of the cathode (black
particles cover).
7
8
9
For some reviews, see: (a) F. M. J. Tappe, V. T. Trepohl and
M. Oestreich, Synthesis, 2010, 3037; (b) C. S. Demmer, N.
Krogsgaard-Larsen and L. Bunch, Chem. Rev., 2011, 111
7981; (c) A. L. Schwan, Chem. Soc. Rev., 2004, 33, 218; (d) S.
Van der Jeught and C. V. Stevens, Chem. Rev., 2009, 109
,
,
2672.
(a) T. Hirao, T. Masunaga, Y. Ohshiro and T. Agawa,
Tetrahedron Lett., 1980, 21, 3595; (b) T. Hirao, T. Masunaga,
Y. Ohshiro and T. Agawa, Synthesis, 1981, 56; (c) H.
Toshikazu, M. Toshio, Y. Naoto, O. Yoshiki and A. Toshio, Bull.
Chem. Soc. Jpn, 1982, 55, 909.
10 (a) M. Kalek, M. Jezowska and J. Stawinski, Adv. Synth. Cat.,
2009, 351, 3207; (b) W. Xu, G. Hu, P. Xu, Y. Gao, Y. Yin and Y.
Zhao, Adv. Synth. Cat., 2014, 356, 2948; (c) O. Berger, C.
Petit, E. L. Deal and J.-L. Montchamp, Adv. Synth. Cat., 2013,
355, 1361; (d) K. Xu, H. Hu, F. Yang and Y. Wu, Eur. J. Org.
Chem., 2013, 319; (e) Y. Belabassi, S. Alzghari and J.-L.
Montchamp, J. Organomet. Chem., 2008, 693, 3171; (f) M.
Kalek, A. Ziadi and J. Stawinski, Org. Lett., 2008, 10, 4637; (g)
E. L. Deal, C. Petit and J.-L. Montchamp, Org. Lett., 2011, 13
,
3270; (h) A. J. Bloomfield and S. B. Herzon, Org. Lett., 2012,
14, 4370; (i) L. J. Gooßen and M. K. Dezfuli, Synlett, 2005,
445.
11 (a) B. Xiong, M. Li, Y. Liu, Y. Zhou, C. Zhao, M. Goto, S.-F. Yin
and L.-B. Han, Adv. Synth. Cat., 2014, 356, 781; (b) J.
Ballester, J. Gatignol, G. Schmidt, C. Alayrac, A.-C. Gaumont
and M. Taillefer, ChemCatChem, 2014, 6, 1549; (c) H. Rao, Y.
Jin, H. Fu, Y. Jiang and Y. Zhao, Chem. Eur. J., 2006, 12, 3636;
(d) C. Huang, X. Tang, H. Fu, Y. Jiang and Y. Zhao, J. Org.
Chem., 2006, 71, 5020; (e) D. Gelman, L. Jiang and S. L.
Buchwald, Org. Lett., 2003, 5, 2315; (f) M. Stankevič and A.
Włodarczyk, Tetrahedron, 2013, 69, 73.
12 (a) Y.-L. Zhao, G.-J. Wu, Y. Li, L.-X. Gao and F.-S. Han, Chem.
Eur. J., 2012, 18, 9622; (b) J. Yang, J. Xiao, T. Chen and L.-B.
Han, J. Org. Chem., 2016, 81, 3911; (c) A. Kinbara, M. Ito, T.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins